


Fanfic Number One Million Of Stiles and Derek's First Time

by where_havealltheflowers_gone



Category: Teen Wolf (TV)
Genre: Anal Fingering, Anal Sex, Based on Reality, Bottom Derek Hale, Boys In Love, Comfort, Established Relationship, Explicit Sexual Content, First Time, Fluff, M/M, Riding, Sexually Experienced!Stiles, Slight Awkwardness, Smut, Top Stiles Stilinski, Virgin!Derek
Language: English
Status: Completed
Published: 2013-07-21
Updated: 2013-07-21
Packaged: 2017-12-20 20:59:22
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,215
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/891792
Author URL: https://archiveofourown.org/users/where_havealltheflowers_gone/pseuds/where_havealltheflowers_gone
Summary: <blockquote class="userstuff">
              <p>Stiles rubbed his cheek on the knee of Derek’s sweats. “So when are we doing the dirty?”<br/>	“Soon.”</p>
            </blockquote>





	Fanfic Number One Million Of Stiles and Derek's First Time

**Author's Note:**

> Soooo, this may be mine and my boyfriend's first time as a Sterek fic.
> 
> But it may not be.. Who knows?
> 
> (hint: you all know. because, second hint: it is)

It didn’t happen the way Stiles originally hoped thought it would.   
He had pictured Derek pushing him against a wall, crushing their lips together, shoving a hand down Stiles’ pants and giving him the best orgasm of his life. Not that what happened didn’t result in the best orgasm of Stiles’ life; it just wasn’t how he’d imagined said orgasm occurring.   
See, Stiles was more of a “go now and discuss why we shouldn’t have done this later” kind of guy. Whereas, Derek, well Derek was more of a “let’s sit and think this out, but never ever talk about it” sort of guy.  
When Derek finally decided he was ready, they weren’t making out or lying in bed like he had thought they would be. It was late, maybe two or three in the morning, and Stiles was stretched out across Derek’s lap. He was dozing in and out, while Derek played lazily with his hair and ran his fingernails all over Stiles’ back, forming random patterns. The TV was droning on in the background, and Derek could feel Stiles’ warm breath ghosting over his knee.  
“Stiles?” he whispered into the darkness, bending slightly to see if the teen was awake.   
“Hm?” Stiles acknowledged drowsily.  
“I’m ready.”  
“Ready for wha?” Stiles asked, not fully awake.  
“Stiles. I’m ready.”   
Stiles pushed himself up to look at Derek’s face. His eyes were only half open and his hair was sticking up in all directions. He slapped his mouth open and shut, tongue clicking the roof of his mouth. “I don’t know what-“ He cut himself off when he saw the look of intent on Derek’s face. “Oh. Oh!” He rubbed his eyes with the back of his hand. “Right now?”  
Derek rolled his eyes. “No, dumbie. Just whenever.”  
“Well, let’s do it now.”  
“You were sleeping.”  
“But now I’m wide awake.” He grinned and shuffled around so he was straddling his boyfriend. He leaned down to peck Derek on the lips. “Sure you’re ready?”  
“I wouldn’t have said I was if I wasn’t. But, seriously, not right now. We don’t have the stuff and I’m tired.”   
Stiles ground his erection into Derek’s. “You don’t feel tired,” he teased.  
“The body responds to stimuli, no matter what a person is feeling emotionally.”  
Stiles groaned in false annoyance. “You sound like a medical textbook.”   
“One would think you’d be proud that I learned something from your feminist rants.”   
Stiles rolled off of Derek. “You’ve officially killed the mood.”  
“By talking about feminism? You love feminism.”  
“Not in a sexual context. I don’t want to talk about politics right now.” Stiles reached over from his place on the couch to run his hand down Derek’s torso. “Can I jack you off?”  
Derek grabbed Stiles’ hand before it could travel under his waistband. “Not tonight.”  
“Please?”  
Derek chuckled while he laced his fingers with Stiles’. “You’re begging to jack me off when I won’t reciprocate?”  
“I wasn’t begging, one. And, two, you would totally reciprocate. Because I’d pout at you, and you’d feel bad.”  
“You’d guilt me into sex?”  
“No! You know I’d never do that.”  
“I was just teasing. I don’t want to talk about sex anymore. Come here.” Derek tugged on Stiles hand, pulling him back down onto Derek’s lap. Stiles twisted so he was in the same position as before. “Go to sleep.”   
Stiles rubbed his cheek on the knee of Derek’s sweats. “So when are we doing the dirty?”  
“Soon.” 

 

‘Soon’ turned out to be three days later.   
They were standing in Derek’s room, Stiles on one side of the bed and Derek on the other, fully clothed and staring at each other across the bed.   
“Take your shirt off,” Derek instructed.  
“You first.”  
Derek rolled his eyes. “We’ll do it at the same time.”   
“Okay,” Stiles reached for the hem of his Justice League shirt, “One, two, three.” He pulled his up and over his head, as Derek did the same. They eyed each other. “Jesus,” Stiles breathed, “You’re sexy.”  
Derek smirked. “You too.”  
“Pants next?”  
Derek nodded. “Leave our boxers on.”  
Pants off, Stiles put a knee on the bed and crawled over to Derek. He wrapped his arms around the older man’s neck. “Kiss me,” he mumbled.  
Derek obliged, hands resting easily on Stiles’ narrow hips. Their tongues slid together in a way that was all too familiar. Stiles lifted his head, allowing Derek to explore the mouth that he already knew so well.  
Stiles broke the kiss, tugging on Derek’s shoulders. “Come down here.”   
Derek did, up on his knees, mirroring Stiles’ position. “How do you want me?” he asked, voice already hoarse.  
“Get on all fours.”  
“Why?”  
“So I can prep you, silly.”  
Derek nodded, bracing his weight on his hands and knees.  
Stiles blanketed himself over Derek’s back, kissing Derek’s hair. “I love you,” he mumbled into it, “You know that, yeah?”  
Derek swallowed, his throat feeling like the Sahara Desert. “Yeah, I know. I love you too.”  
Stiles kissed his head again. “Good.” He shifted slightly so he could press his lips against the back of Derek’s neck. He moved again to kiss Derek’s shoulder. He kept moving his lips down and down, kissing each knot in Derek’s spine, nipping at his lower back. “You ready to take these off?” he asked as he hooked his fingers into Derek’s boxers.  
“I guess.”  
Stiles paused. “You guess? Lovin’ the enthusiasm.” He laid over Derek’s back, looking down at his face. “Look at me. What’s wrong?”  
Derek shrugged. “Nervous.”   
Stiles nodded slowly. “Lie down,” he said as he patted Derek’s bicep. He rolled off long enough for Derek to do as he said, then he got on top again, straddling Derek’s lower back. He reached down to rub Derek’s neck.   
“Stiles,” Derek muttered after a moment, “What are you doing?”  
Stiles moved his hands over to Derek’s shoulders. “You’re tense, baby. Just helping you relax.”  
“You don’t have to.”  
“Sure I do. Keeping you happy is sort of my job. Now, shush. Close your eyes. Relax.”  
A few minutes later, after Stiles was sure Derek had loosened up, he slid off and laid down next to Derek, a hand tangled in his boyfriend’s hair. “We don’t have to do anything you’re uncomfortable with,” Stiles whispered, his face only inches from Derek’s.  
“I want to do this. With you. I’m completely comfortable with you. We’re doing this. I said we would, and we are.”  
Stiles shook his head. “You can back out whenever you need to. It doesn’t matter what you said. I won’t be disappointed.”  
“Yes, you would.”  
“No,” Stiles objected, “I really won’t be. This isn’t about what you promised or what I expect. This is about trusting each other.”  
“I trust you.”   
“Promise?”  
“Promise.”  
“You good to keep going?”  
Derek nodded. “I feel good. Thank you.”   
Stiles grinned. “No problem, dude.” Stiles let his hand move from Derek’s hair, lower and lower until it was eventually cupping his ass. Derek moaned when Stiles squeezed lightly. “You like that?”  
“Yes,” Derek moaned. “Stiles, please.”  
“I got you, don’t worry.” Stiles sat up, leaning over to the bedside table to grab the lube. “Want me to take these off now?”  
Derek lifted himself up onto his elbows and knees again. “Please.”  
Stiles tugged Derek’s boxers off, having Derek lift his legs so he could slide them off completely. “You good?”  
“I’ll be good when you do something.”  
Stiles chuckled. “Snarky as always, my love.” Stiles ran his hands up and down Derek’s sides, enjoying the noises of contentment Derek was making.   
“Stiles,” Derek ground out through gritted teeth, “Do something.”  
“Easy there, friend. We’re doing this shit right.”   
“Just get on with it.”  
“Fine, fine.” Stiles coated his index finger with lube and ran it around Derek’s hole. Derek sucked in his breath. “Everything okay?”  
“Lube’s cold,” Derek mumbled.   
Stiles hummed noncommittally. “You ready?”  
Derek nodded and swallowed. “Yeah,” he said, “Yeah, go ahead.”  
Stiles slowly pushed his finger into Derek, pausing when the older man gasped. He wiggled it slightly, causing Derek to whimper low in his chest. “Good or bad?”  
“Good,” Derek huffed, “Really good. Weird, but good. Don’t stop.”  
“Lemme know if you need a minute, okay?” Stiles rested his hand on Derek’s hip and pressed a little more. He got up to the second knuckle and twisted his finger to the right.   
Derek moaned, loud and filthy. “I can take more,” he gruffed.  
“You’re sure?”  
Derek swung his head to side so he could look at Stiles. “I think I know my own limits.”  
“Aright, alright. Just trying to look out for you, sweetcheeks.” Stiles smiled at him, “I mean that nickname literally right now.”  
Derek dropped his head, letting it hand between his arms. “You would make jokes during sex.”  
“Would you love me if I were any other way?”  
“I would love if you would put another finger inside of me.”  
Stiles clicked his tongue. “So blunt.” He pulled his finger out, lubing two of them up and slowly inserted them again. Derek’s whining caused Stiles to stop. “Okay?”  
“Just a second,” Derek panted softly, “Spread them.”  
“Are you sure because-“  
“Just do it,” Derek barked.  
“I don’t want to hurt you.”  
“It feels good. I told you to stop so I wouldn’t come.”  
“Oh, well. Okay then.” Stiles pushed the fingers so they were mostly in and scissored them. Derek groaned. “My god,” Stiles mumbled, “You’re so tight and hot. This is so hot. I might come in my pants.”   
“I might come like this,” Derek admitted, “Give me another.”  
“Are you-“ Derek’s glare cut off Stiles’ words. “Look, I’m just making sure you’re okay.”  
“I’m fine. Just do it.”  
“You win more flies with honey than with vinegar,” Stiles scolded. He lubed his third finger and shoved it in roughly, separating them almost immediately.   
“Could have given me a warning,” Derek gasped.  
“That’s what you get for being mean to the guy with his fingers in your ass.”  
“I’m sorry,” Derek said, locking his eyes with Stiles’.  
Stiles shrugged. “S’ okay. I sort of like how slutty you’re being.”  
Derek bit his lip, suppressing the moan that threatened to escape. He dropped his head again. “I’m ready,” he said after a minute or two.   
“Okay,” Stiles said, “How do you want to do this?”  
Derek looked back, teeth worrying over his lip. “Can I ride you?”  
“Hell yeah!” Stiles whooped, reaching down to shuck off his boxers. He crawled up the bed, pressing a soft kiss to Derek’s lips, and settled himself against the headboard. “Toss me the lube.” Derek rocked back on his heels, and the lube came flying, smacking the wall behind Stiles’ head. “Careful!”   
Derek smirked playfully, “Sorry.”  
Stiles poured lube into his hand. “Liar,” he smirked back. He hissed as he rubbed the liquid onto his hard-on. “Ready when you are,” he said, chucking the bottle to the side.   
Derek scuttled up, settling with a leg on each side of Stiles’ lap. He braced his hands on the headboard of the bed, and lowered himself onto Stiles’ dick. The head of it was in, and he stopped, breathing through the stretch and burn.  
“Holy shit,” Stiles murmured beneath him. “You alright? We can stop, if you need to.”  
“M’ fine. Just need a minute to adjust.”  
“Does it… I mean, how does it feel?”  
“Good,” Derek said, taking more of it into himself, “Really good.”  
“Not gonna last long,” Stiles panted.  
“Me neither,” Derek grunted and sank down all the way.   
“Oh my god,” Stiles moaned, tossing his head back against the wall.   
Derek rocked his hips and groaned, moving his hands so he could grasp Stiles’ shoulder.   
Stiles let his hands settle on Derek’s thighs. “Jesus Christ,” he mumbled, “You’re so… perfect. Holy shit.”  
Derek picked himself up and slammed back down. “You feel so good,” he groaned as he rolled his hips again.  
“Holy fucking… oh god, don’t stop doing that.”   
“Stiles,” Derek moaned, “I need- Can you-“  
“I got you, baby, I got you.” Stiles reached down between them, catching Derek’s hard cock in his hand. He yanked once, twice and Derek was coming, head thrown back and mouth open in a silent cry. The sight sent Stiles over the edge unexpectedly, and he bucked into Derek’s ass as he came, moaning and mumbling praises that he didn’t remember later. 

 

“Was it good for you?” Derek asked hours later as they were lying naked in bed. He was on his stomach, arm stretched out so Stiles could use it as a pillow.  
The hand on his abs stilled. “It was perfect for me,” Stiles assured. “You?”  
Derek shifted onto his side, arm draped over Stiles’ hip. “Perfect,” he mimicked.   
“Really? Or are you just saying that?”  
Derek brushed hair from Stiles’ eyes. “Have I ever lied to you?”  
“No,” Stiles smiled, “No, you never have.”  
“And I never will. It was perfect.”  
“Was it everything you imagined?”  
“No,” Derek said, “It was better.” He pulled Stiles to his chest, arms wrapped around his back securely.   
Stiles nuzzled into Derek’s neck. “Good. I’m really glad.”  
“Hey, Stiles?” Derek raked his hands over Stiles’ back.   
“Yes, dear?”  
“I love you.”  
“Hmm, Stiles hummed happily, “I love you too.”

**Author's Note:**

> Come tumble with me: 
> 
> http://where-havealltheflowers-gone.tumblr.com


End file.
